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  • Title: Inhibitors of sterol synthesis: 3 beta-hydroxy-25,26,26,26,27,27,27- heptafluoro-5 alpha-cholestan-15-one, an analog of a potent hypocholesterolemic agent in which its major metabolism is blocked.
    Author: Swaminathan S, Siddiqui AU, Pinkerton FD, Gerst N, Wilson WK, Schroepfer GJ.
    Journal: Biochem Biophys Res Commun; 1994 May 30; 201(1):168-73. PubMed ID: 8198571.
    Abstract:
    The chemical synthesis of 3 beta-hydroxy-25,26,26,26,27,27,27-heptafluoro- 5 alpha-cholestan-15-one (IV) has been pursued to provide an analog of the potent hypocholesterolemic agent 3 beta-hydroxy-5 alpha-cholest-8(14)-en-15-one (I) in which its major metabolism is blocked. Reduction of 3 beta-acetoxy-5 alpha-chola-8(14),23-dien-15-one with lithium in liquid ammonia gave 3 beta-hydroxy-5 alpha-chol-23-en-15-one (VI). Addition of (CF3)2CFI to VI in the presence of triethylborane gave 3 beta-hydroxy-23R-iodo-25,26,26,26,27,27,27-heptafluoro-5 alpha-cholestan- 15-one, which was reduced to IV with tributyltin hydride. IV was found to be highly active in lowering the levels of HMG-CoA reductase activity in CHO-K1 cells, in lowering acyl coenzyme A:cholesterol acyltransferase activity in jejunal microsomes, and in lowering serum cholesterol levels in rats.
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